25
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Preparation of Cyclic 3′,5′-Phosphoramidites and -Amidates of Antiviral and Antitumor 5-X-2′-Deoxyuridines (X = H, CH3, I, F, CF3, trans-CH=CHBr)

, , &
Pages 1359-1367 | Received 22 Jan 1989, Published online: 24 Oct 2006

References

  • Oxford College of Emory University, Oxford, GA 30267
  • Revankar , G. R. and Robins , R. K. 1982 . In Handbook of Experimental Pharmacology , Edited by: Nathanson , J. A. and Kebabian , J. W. Vol. 58/I , 17 – 151 . Berlin and Heidelberg, , West Germany : Springer-Verlag . For a review see
  • Van Haastert , P. J.M. and Kien , E. 1983 . J. Biol. Chem. , 258 : 9636
  • Béres , J. , Bentrude , W. G. , Balzarini , J. , De Clercq , E. and Otvos , L. 1986 . J. Med. Chem. , 29 : 494
  • Béres , J. , Sagi , G. , Bentrude , W. G. , Balzarini , J. , De Clercq , E. and Otvös , L. 1986 . J. Med. Chem. , 29 : 1243
  • Nelson , K. A. , Bentrude , W. G. , Setzer , W. N. and Hutchinson , J. P. 1987 . J. Am. Chem. Soc. , 109 : 4058
  • Sopchik , A. E. and Bentrude , W. G. 1981 . Tetrahedron Lett. , 22 : 307
  • Bentrude , W. G. and Setzer , W. N. 1987 . P NMR Spectroscopy in Stereochemical Analysis: Organic Compounds and Metal Complexes , Edited by: Verkade , J. G. and Quin , L. 365 – 389 . Deerfield Beach, FL : VCH Publishers, Inc. .
  • Sopchik , A. E. , Bajwa , G. S. , Nelson , K. A. and Bentrude , W. G. 1981 . Phosphorus Chemistry , ACS Symposium Series, No. 171 Edited by: Quin , L. D. and Verkade , J. G. 217 – 220 . Washington, D.C. : American Chemical Society .
  • Gerlt , J. A. and Coderre , J. A. 1980 . J. Am. Chem. Soc. , 102 : 4531 Baraniak, J.; Lesiak, K.; Sochaki, M.; Stec, W.J. Ibid. 1980, 102, 4533
  • Eberle , M. K. and Brzechffa , L. 1988 . Nucleosides Nucleotides , 7 : 117
  • Bottka , S. , Pelczer , I. and Tomasz , J. 1988 . Nucleosides Nucleotides , 7 : 137
  • Bottka , S. and Tomasz , J. 1988 . Nucleosides Nucleotides , 7 : 307
  • Bottka , S. and Tomasz , J. 1985 . Tetrahedron Lett. , 26 : 2909
  • Bentrude , W. G. and Tomasz , J. 1984 . Synthesis , : 27
  • Béres , J. , Bentrude , W. G. , Parkánji , L. , Kalman , A. and Sopchik , A. E. 1985 . J. Org. Chem. , 50 : 1271
  • Baraniak , J. and Stec , W. J. 1987 . J. Chem. Soc. Perkin Trans. 1 , : 1645
  • Sopchik , A. E. and Bentrude , W. G. 1980 . Tetrahedron Lett. , 21 : 4679
  • Bentrude , W. G. , Sopchik , A. E. , Setzer , W. N. , Bates , R. B. and Ortega , R. B. 1986 . Acta Cryst. , C42 : 584
  • Bajwa , G. S. and Bentrude , W. G. 1978 . Tetrahedron Lett. , : 421
  • Bajwa , G. S. and Bentrude , W. G. 1980 . Tetrahedron Lett. , 21 : 4683 Bentrude, W.G.; Sopchik, A.E.; Bajwa, G.S.; Setzer, W.N.; Sheldrick, W.S. Acta Cryst. 1986, C42, 1027
  • Sopchik , A. E. and Bentrude , W. G. 1981 . Tetrahedron Lett. , 22 : 307
  • Gajda , T. M. , Sopchik , A. E. and Bentrude , W. G. 1981 . Tetrahedron Lett. , 22 : 4167
  • Baschang , G. and Kvita , V. 1973 . Angew. Chem. Intern. Ed. English , 12 : 71 The preparation of 2b is modeled after that of An exceptionally high but atypical yield of 2b (38%) was reported in ref 5a.
  • De Clercq , E. 1985 . Nucleosides Nucleotides , 4 : 3 Heidelberger, C.; Danenberg, P.V.; Moran, R.G. Adv. Enzymol. 1983, 54, 57
  • The benzyl phosphate cyclic triester of 3a showed cytostatic activity against Raji human lymphoblasts comparable to that of the cyclic diester (ref. 4b)
  • Stec , W. J. and Zielinski , W. S. 1980 . Tetrahedron Lett. , 21 : 1361
  • Newton , M. G. , Pantaleo , N. S. , Bajwa , G. S. and Bentrude , W. G. 1977 . Tetrahedron Lett. , : 4457
  • We earlier showed 7h,i that a mixture of cis- and trans-3b prepared from reaction of 1.0 g of 4 with Me2NCl can be separated in a single pass on an MPLC column to give 200 mg of cis-3b and 500 mg of trans-3b. (15 × 1000 mm column of Merck 230–400 mesh Si02; CHCl3/CH3OH, 97/3)

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.